Do you have specific Tweet IDs that appear not to include images when they should have done so? It is not very clear from the screenshot you’ve shared here what is going on. Can you explain exactly what your code is doing and why you believe images are “not sent”?

The tweet missing the image (the first one in my screenshot) is https://twitter.com/DayZ/status/1082894742512431104
My code is looking for the extended_entities key, then the media key, and if both are present it iterates over the media array. Then, if the media checked is a photo, it removes the media’s url from the tweet text and adds an image to a Discord richembed (you can see two differents RichEmbeds in my screenshot, with the blue left border), then send the said richembed in a Discord channel.
I also tried with thetweet_mode=extended parameter, did not fixed it.

I just added extra logging as I can’t reproduce if I follow my own account and tweet images, so I can provide you more infos

I’ve just retrieved that Tweet ID using tweet_mode=extended and the media entities show up as expected. Note that, for Tweets from the Streaming API, this parameter does not work; instead, the API serves up both versions of the Tweet in the same object. You should be able to find the extended Tweet content inside the main Tweet.